benzyl N-(1-hydroxy-4-phenylbutyl)carbamate | 197173-25-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-(1-hydroxy-4-phenylbutyl)carbamate
• CAS: 197173-25-4
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: WOFJMWLRQPFEOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl N-(1-hydroxy-4-phenylbutyl)carbamate 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到(1,2,3,4-tetrahydronaphthalen-1-yl)carbamic acid benzyl ester
  参考文献：
  名称：

  Efficient generation and intramolecular cyclization reactions of acyl imines

  摘要：

  Acyl carbamates can be selectively reduced with diisobutyl aluminum hydride to provide high yields of N-acyl hemiaminals 1. With appropriate substitution, these intermediates undergo Lewis acid catalyzed intramolecular exo cyclization reactions to afford l-amino 1,2,3,4-tetrahydronaphthalene derivatives. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01531-1
• 作为产物：
  描述：

  4-苯基丁酰氯 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 benzyl N-(1-hydroxy-4-phenylbutyl)carbamate
  参考文献：
  名称：

  The Preparation and Intra- and Intermolecular Addition Reactions of Acyclic N-Acylimines:  Application to the Synthesis of (±)-Sertraline

  摘要：

  Intramolecular endo-cyclization reactions of N-acyliminium ions have seen wide application for the synthesis of heterocyclic compounds. The corresponding exocyclic variant, which would provide 1-aminotetralin derivatives, for example, has little precedent. We have discovered that acyclic N-acylcarbamates can be readily reduced to the corresponding N-acylhemiaminal derivatives in high yield using DIBAL as the reducing agent. These intermediates are remarkably stable and, if desired, can be purified and stored. The acyclic N-acylhemiaminals undergo both intra- and intermolecular nucleophilic addition reactions mediated by strong Lewis acids, such as TiCl4. Diastereoselectivity, induced either by a substituent on the newly formed ring, or by utilizing a chiral ester on the carbamic acid, was disappointingly low. This methodology was successfully applied to the synthesis of the racemic form of the marketed antidepressant sertraline.

  DOI：

  10.1021/jo010370l

文献信息

• Efficient generation and intramolecular cyclization reactions of acyl imines
  作者：Michael P. DeNinno、Cynthia Eller

  DOI：10.1016/s0040-4039(97)01531-1

  日期：1997.9

  Acyl carbamates can be selectively reduced with diisobutyl aluminum hydride to provide high yields of N-acyl hemiaminals 1. With appropriate substitution, these intermediates undergo Lewis acid catalyzed intramolecular exo cyclization reactions to afford l-amino 1,2,3,4-tetrahydronaphthalene derivatives. (C) 1997 Elsevier Science Ltd.
• The Preparation and Intra- and Intermolecular Addition Reactions of Acyclic <i>N</i>-Acylimines:  Application to the Synthesis of (±)-Sertraline
  作者：Michael P. DeNinno、Cynthia Eller、John B. Etienne

  DOI：10.1021/jo010370l

  日期：2001.10.1

  Intramolecular endo-cyclization reactions of N-acyliminium ions have seen wide application for the synthesis of heterocyclic compounds. The corresponding exocyclic variant, which would provide 1-aminotetralin derivatives, for example, has little precedent. We have discovered that acyclic N-acylcarbamates can be readily reduced to the corresponding N-acylhemiaminal derivatives in high yield using DIBAL as the reducing agent. These intermediates are remarkably stable and, if desired, can be purified and stored. The acyclic N-acylhemiaminals undergo both intra- and intermolecular nucleophilic addition reactions mediated by strong Lewis acids, such as TiCl4. Diastereoselectivity, induced either by a substituent on the newly formed ring, or by utilizing a chiral ester on the carbamic acid, was disappointingly low. This methodology was successfully applied to the synthesis of the racemic form of the marketed antidepressant sertraline.